


Meet the New Boss

by jensenisafallenangel



Category: Supernatural
Genre: Alternate Universe - Office, Anal Sex, Angry Sex, Bathroom Sex, Bisexual Dean Winchester, Boss/Employee Relationship, Bottom Castiel, Bottom Dean, Christmas Party, Deansturbation, Dirty Talk, Explicit Sexual Content, Frottage, Helpful Sam, Jealous Castiel, Jealousy, Love Confessions, M/M, Office Blow Jobs, Office Sex, Porn With Plot, Possessive Castiel, Rough Sex, Semi-Public Sex, Sexual Tension, Switching, Top Castiel, Top Dean
Language: English
Status: Completed
Published: 2015-10-07
Updated: 2015-11-05
Packaged: 2018-04-25 06:34:38
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 4
Words: 12,153
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/4950307
Author URL: https://archiveofourown.org/users/jensenisafallenangel/pseuds/jensenisafallenangel
Summary: <blockquote class="userstuff">
              <p>Dean is not happy. His new boss is the frustratingly sexy Castiel Novak who he does not and cannot like. Their tension builds and builds until the dam bursts. Can it be more than just angry sex?</p>
            </blockquote>





	1. Breaking In The New Office

**Author's Note:**

> I tried to combine what we all love about classic Dean Winchester with the Dean Smith I needed for an office AU. Enjoy the combination!
> 
> Any relationships besides Dean/Cas are very very minor so if that's what brought you here...sorry. I just tagged it because it's there just not huge.
> 
> Bottom!Dean/Top!Cas is Ch 2  
> Bottom!Cas/Top!Dean is Ch 1 & 4

Dean Winchester straightened his tie with one hand as he closed the door to the conference room he was exiting. He was fairly certain the interview had gone well.

Sitting on a chair in the hallway was Castiel Novak, essentially his rival at the office and probably his least favorite person. The guy was snooty and seemed to hate fun. Dean wasn’t even sure he had seen the guy smile. Ever. They had been hired around the same time so Dean had known him for a couple of years.

Dean caught Castiel’s eye and gave him a wink in an effort to throw him off before his own interview then walked away.

Their boss, Zachariah Adler, was getting promoted since whoever was above him in the corporate food chain was retiring. Dean and Castiel were competing just like they always were. Only this time the stakes were much higher. More responsibility but more pay, plus considerable bonuses with an amazing corner office and a better parking spot.

Dean went back to his decently-sized office he currently had and kept working. He wasn’t being considered for the promotion because he slacked off. 

Once he got home after the work day was done, he poured himself a drink after a balanced and healthy dinner. Then, he called his brother like he always did when he was stressed.

“How’d it go?” Sam said right when answered the phone. 

“Hi to you, too,” Dean laughed. “I think it went pretty well.”

“Good. I’m sure it did, they love you there.”

They caught up since it had been a while since they really got to talk. Dean had previously shot him a quick text about the interview and how it was against Castiel so he was a little nervous. If anyone in the office had a better work ethic than Dean, it was Castiel frickin’ Novak.

Dean said as much to his brother.

“No way he works harder than you,” Sam defended his brother, “I practically have to make an appointment just to talk to you."

Dean felt bad he didn’t talk as much with his brother as he would like but he was hoping all of the hard work and sacrifice would be worth it if he could snatch Zachariah’s job.

“I’ll let you know how it goes when I know and we’ll talk again soon,” Dean ended.

“Sounds good,” Sam responded. “Bye Dean.”

A week later, the higher-ups finally had an announcement on who got the job.

Dean didn’t get it. 

That put him in a crappy mood and it didn’t help when he got an e-mail from his new boss, Castiel Novak, who wanted to see him in his office as soon as possible. 

Dean let out an annoyed groan before shoving his chair back from his desk. If he was meeting up with that stuck-up snob, he needed his coffee first.

He grabbed some and downed it before heading upstairs where Castiel’s new office was. 

Dean knocked and reminded himself to try to be a good sport about the whole thing since, unfortunately, this was who he had to answer to now.

“Come in,” Castiel responded.

Dean pushed open the door and walked in. It was definitely bigger than Dean’s office and it had a couch and everything. It was in the corner with a wonderful view that had Dean gritting his teeth in envy. Being civil was going to be harder than he thought.

“Hello, Dean,” Castiel greeted. “Would you like to sit down?”

Dean was still in a bad mood about how the whole thing turned out and was not kind in his reply.

“What do you want?” Dean snapped, not sitting down.

“Is that any way to talk to your new boss?” Castiel asked, sounding more threatening than Dean had ever heard him.

Dean bit the inside of his cheek so he wouldn’t answer and get in trouble. His question still stood. 

“I wanted to make sure there weren’t any hard feelings about how the promotion turned out and I suppose you just answered that for me,” Castiel said, his blue eyes set in a steely gaze.

Dean still didn’t answer and glared back just as hard.

“I need these done by tomorrow,” Castiel said, pushing a manila folder across his desk.

Dean picked the file up.

“Is that all?” Dean said before adding a snarky “sir.”

Castiel gave one curt nod. 

“You may go,” Castiel said with finality.

Dean didn’t need to be told twice. 

In his own office, Dean threw the folder on his desk and few papers spilled out. It was a bunch of spreadsheets and documents he needed to go over and complete before a huge meeting they had with a potential client tomorrow.

As he paced angrily, he considered not doing them. If he didn’t finish the prep work for this, Castiel would already look bad since someone under him didn’t do their job. But Dean knew Zachariah as a boss and he would hold Dean accountable for his own work, not Castiel. 

There was no way out of doing this so he sat down and got to work. He ended up having to stay extremely late to finish and was in a sour mood as he drove home to his empty apartment.

He shot a quick text to Sam saying Castiel was the worst boss ever before going to take a shower. Maybe “worst” was an exaggeration since Zachariah had the position before him and was awful but that didn’t make Dean feel better about the situation.

At least Castiel was better to look at, Dean reasoned. The guy’s dark hair was all over the place and his blue eyes were magnetic. Dean had thought about Castiel like this before, how hot he was, but it was impossible to do something about it since they worked together and now Castiel was Dean’s boss. There was that plus the fact that the guy was a prick.

Dean stood under the warm water and wrapped his hand around his gradually hardening cock, thinking of Castiel giving him orders and bending him over his nice, new desk with the curtains wide open for anyone to see.

“Fuck.” 

Dean let out the word as a groan, pumping himself harder. He wanted to have Castiel in the shower with him, those pink lips sucking him off and swallowing him down. Dean would tangle his hands in his hair and tell him how good he looked taking his cock. 

A few more thrusts into his hand and Dean came with a shout of Castiel’s name.

 

The next morning was the big meeting. Dean had all of his pages ready to go and he was confident Castiel would be pleased with how they turned out. Pleasing Castiel sent an unnecessary shiver down Dean’s spine as he took the elevator up to the conference room. He cleared that thought away and reminded himself he needed to focus.

The meeting went well and Dean almost saw a smile on Castiel’s sinfully good-looking lips. Almost.

After the meeting, Castiel asked Dean to stay back for a second.

“What’s up?” Dean asked. 

He was in a good mood since his hard work paid off so he didn’t mind talking to his boss.

“You did a good job, Dean,” Castiel said.

Dean tried to keep his thoughts clean but hearing the praise from Castiel had him a little flushed.

“Thanks,” Dean grinned.

This was probably the most civil they had been towards each other since they met and Dean was waiting for it to go south.

“Zachariah thinks we would work well together and has assigned us to keep doing the work for this client,” Castiel explained.

There it was.

“Seriously?” Dean asked.

Castiel knit his eyebrows in confusion and tilted his head.

“He was our boss for a long time and he knows we don’t get along!” Dean pointed out. 

“That is categorically untrue,” Castiel tried, crossing his arms.

“Our second week here, I unscrewed the lid on the salt when I knew you would use it in the break room and put a whoopee cushion on your seat in the conference room during a huge meeting and Zachariah got pissed at you instead of me. So then you kept lowering the chair in my office since you knew I kept it at just the right height and told most of the women here that I am into nurse roleplay,” Dean commented. “Oh, and you hid my car keys. Twice.”

“You don’t know that was me!” Castiel said defensively, his eyes narrowing dangerously.

“Who else would do all of that?” Dean asked, taking a step towards Castiel.

“It doesn’t matter,” Castiel snapped. “This went well and we have to work together, whether you like it or not.”

“Fine,” Dean snapped back.

“Fine,” Castiel repeated.

Dean was torn between slapping Castiel and kissing him, which happened a lot. They continued glaring and Dean was going to make a flippant remark when the door to the conference room opened.

“Uh, Mr. Novak? Mr. Adler wants to see you,” the man said.

“Thank you,” Castiel replied, his eyes not leaving Dean.

The man left, shutting the door behind him.

“Meet me after lunch and we can get working,” Castiel said.

“Yes, sir,” Dean answered with a sarcastic eye roll before walking out of the room.

Dean took his time getting something to eat from the cafeteria and eating it slowly at his desk. He wished for a burger but the only thing with meat was a chicken salad so he had to settle. 

Then, he practiced his putting on a little green he had set up in his office. Truth be told, his short game was improving. At the next company outing, Dean would be sure to place some bets on himself to win.

Once it hit two-thirty in the afternoon, he sauntered upstairs to Castiel’s office. He knocked on the door and already knew his boss would be angry.

“Come in.” 

Dean heard Castiel and entered the office.

“You’re late,” Castiel said without looking up from his computer. 

“No,” Dean smirked. “You said after lunch. Correct me if I’m wrong but it is after lunch, right?”

That got Castiel’s attention. He looked up, opened his mouth to say something, and shut it again. 

Dean’s smirk got even wider. He accepted a handful of documents from Castiel and sat down on his black, leather couch. After he spread the documents on the coffee table in front of the couch, he took off his suit jacket and threw it on the arm of the couch. Next, he rolled up his sleeves and loosened his tie just a little. Dean was very aware of Castiel’s eyes on him the whole time.

“Enjoying the show, Cas?” Dean couldn’t help but tease.

Castiel cleared his throat and got back to work while Dean grinned to himself, counting it as a small victory. Dean knew he rocked the rolled-up sleeves and had no shame flaunting himself in front of Castiel and distracting him. It was rather enjoyable.

Dean’s mind wandered to similar thoughts he had last night in the shower but he had to ignore them. He really didn’t want to pop a boner in his boss’s office, especially when he didn’t like him. He just thought he was hot. Stupid Cas with his distracting…everything.

He must have been staring because Castiel looked up from his desk and Dean quickly looked down. Now he was caught staring just like he caught Cas doing. Crap.

They kept working in near silence, just the occasional cough or shuffling of papers. Dean normally liked music when he worked but this wasn’t his office. It hit him that he could probably be doing this work in his own office but he didn’t get a chance to point that out.

“Mr. Novak, will that be all for the day?” his assistant stuck his head in.

“Yes. Thank you,” Cas dismissed.

Dean checked his shiny, silver watch and saw that it was already five and he had made decent progress despite thinking about and looking at Cas too much.

“Can I go too, Mr. Novak?” Dean joked, laying on a fake, sticky sweet voice.

“Dean, when we’re done then you may go,” Castiel answered, glaring like always.

“All right, boss. It was just a joke,” Dean said, throwing his hands up. 

An hour later, Dean figured that they had been working long enough especially since he had stayed so late working the night before getting ready for their meeting that morning.

Dean stood and started gathering his paperwork back into the file they came in. 

“Dean, where are you going?” Castiel asked.

“Home,” Dean answered simply.

“I didn’t say you could leave,” Cas replied, leaning back in his chair and looking content with himself.

“I know you probably get off on giving orders and whatnot,” Dean snapped, watching Cas’s face darken, “but I’m leaving. We can pick this up first thing tomorrow morning.”

“Dean,” Cas said, low and dangerous while he stood up. 

Dean pretended that hearing his name in that voice wasn’t stirring something in him. 

“What, Cas?” Dean responded.

“We aren’t done here,” Cas insisted.

“Oh, I think we are,” Dean answered. “So unless you plan on making me stay…”

Dean’s voice trailed off as he watched Cas stride towards him. 

“I can make you stay,” Cas said quietly. 

It was so quiet, Dean wasn’t even sure he had heard him correctly.

“Yeah?” Dean breathed, a little nervous at how close Cas was standing to him. 

Cas held Dean’s tie in his hand and looked into his eyes, both of their pupils blown with lust. For all their joking around, Dean didn’t think Castiel actually wanted anything like this.

“What are you waiting for?” Dean asked daringly. “Make me stay.”

He had his bravado back and it worked. Cas pulled him in by his tie and crashed their mouths together. It wasn’t perfect but it felt damn near close to it despite being a little sloppy in its haste. 

The kiss was rough, all bruising with passion and a little bit of anger. Dean wasn’t one to turn down angry hate sex though. Even if it was with his infuriating boss.

Dean pushed off Cas’s suit jacket and tossed it aside before backing them up against Cas’s desk. There, he could get more friction and rolled his hips against him. Cas let out a groan into Dean’s mouth so he did it again. Dean had a hand tangled in Cas’s hair and one digging into his hip but moved both to get Cas’s tie off. 

Once the tie was cast away, Dean gently kissed down Cas’s jaw and neck. He was sure Cas didn’t want marks that would be visible so he waited until he got to his collarbone to leave a couple hickeys. 

Dean kept his mouth moving down, licking at each of Cas’s nipples before trailing down his stomach and stopping at the top of his belt. 

“You sure?” Dean asked.

Cas nodded.

“Use your words, sweetheart,” Dean grinned.

“Yes. Dean, please,” Cas begged.

“Much better,” Dean praised. 

Dean undid Cas’s belt and unbuttoned his pants to pull them and his briefs down to his ankles to free his cock. Dean slid his hands around to cup Cas’s ass and lifted him onto his desk. Cas was on the edge of the desk so Dean could squeeze their bodies together and they kissed again, just as roughly as before.

Cas let his hands roam to grab Dean’s ass before moving around to undo Dean’s belt and let his cock out. This time when Dean leaned in to kiss Cas, their throbbing naked erections finally rubbed together.

“Fuck,” Cas groaned.

“Do you have…”

“Drawer,” Cas answered and pointed.

“Wow, really? In the office?” Dean asked, eyebrows raised.

Cas shrugged, looking bashful.

“I’m shocked but glad, boss,” Dean grinned.

Dean grabbed the lube and thoroughly coated their dicks in it, taking them both in his hand. He angled Cas back so he was propped on his elbows, ass on the edge of his desk still, cock pointed towards his stomach. Dean lined his own cock on top of Cas’s, also pointed at Cas’s stomach.

“I’m gonna jerk us both until we come. You’re gonna paint that sexy body of yours, got it?” Dean asked, low and in Cas’s ear. He started slowly moving his hand.

Cas just let out a moan that sounded like Dean’s name.

“Words, babe.”

“Yes, fuck. I want to, please,” Cas replied, his voice hoarse.

Dean smirked and sped up his pace. 

“You were watching me work all night, you wanted this. Right?” Dean said, sucking more marks around Cas’s collarbone out of sight. 

“Yes, wanted you Dean,” Cas said, head thrown back.

Dean pulled Cas even closer to him, sped up and felt his orgasm building.

“You close?” Dean asked. “Fuckin’ close, come with me Cas.”

Cas dug his nails deeper into Dean’s shoulder and hip and bit his lip as he groaned Dean’s name.

“That’s it, I got you. Keep saying my name and I’m gonna…”

“Dean…”

That was enough to make Dean come, hot spurts shooting onto Cas’s tan chest. Cas was right behind him, very nearly shouting Dean’s name. His come got all the way up onto the lovebites Dean had left.

“Holy shit,” Cas said breathlessly.

Dean nodded his agreement but didn’t know what else to say. He felt like some line was crossed and now they were no longer just boss and subordinate. This pushed the envelope and Dean was afraid that Cas would freak out. 

So, he left before that could happen.

He tucked himself into his pants, put on his suit coat and grabbed his papers. He spared a backwards glance at Cas who hadn’t moved and was looking at him with an unreadable expression. Dean’s cock, though spent, gave an interested twitch seeing Cas with his cock still out and chest still heaving and covered in come. 

Dean opened his mouth to say something but decided against it. He shut the door and was gone.


	2. Hotel

**Summary for the Chapter:**

> Dean and Cas go on a business trip.

Dean was not freaking out. It wasn’t like he had to go to a meeting first thing in the morning where his boss would be. The same boss he had made come all over himself the night before. 

Thinking about Cas and the state he left him in, all disheveled and mostly naked, got Dean all hot and bothered again. He loosened his tie a little and took a deep breath, waiting for the elevator to finally stop going up. This meeting had to go well and he needed to absolutely not think of how good it felt to kiss Cas, to mark him up and to hold their cocks together while bringing them both over the edge.

Fuck, Dean thought.

He needed to get his shit together.

As he got to the door to the conference room, he took another deep breath in an attempt to calm down. He opened the door and stepped in.

Cas was just about to get started with the meeting and stood as Dean walked in. Cas pointedly did not look at Dean who took his seat as far away from Cas’s as possible and on the opposite side of the table. The rest of their team was presenting their work to Cas as they waited for their client to arrive.

The meeting did end up going well and afterwards Dean was going to try to talk to Castiel. It seemed like the time to talk, even if he didn’t normally talk about these things. “Love em and leave em” was more of his mantra. However, they were going to be working together a lot and had to move past this. It was once, it didn’t have to happen again and they just had to talk that out. 

Right when the meeting ended, Cas left the room in a seemingly huge rush. Dean decided to suck it up and followed him to his office.

Not stalking, Dean told himself. We need to talk, he reasoned.

Once he got there, Cas’s assistant said that Mr. Novak wasn’t allowing any interruptions. Back at his own desk, Dean found a newly sent e-mail from Cas very formally detailing the work they had to do and what was expected of Dean. 

Dean took that to mean that they wouldn’t be working together in Cas’s office. Fine. If Cas was going to ignore him, that was fine. Dean was bigger than that and he could get over it.

The problem was that Dean was very distracted. He couldn’t just get over what had happened. It didn’t have to mean anything but they should clear the air and be on the same page about it. He tapped his pen on the edge of his desk then threw it down and took to pacing. 

Why would Cas ignore him? Was he embarrassed? Dean knew he was the one that left without saying anything but that didn’t mean Cas had to ignore him. Dean had been... scared wasn’t the word. Dean Winchester didn’t get scared about the thought of emotional attachment. He just avoided it all together.

Even a quick round of putting didn’t quiet his overactive brain.

Whatever, Dean thought. 

There was no way this would have a negative impact on his work. He wouldn’t let Castiel get the satisfaction. Dean wasn’t going to let Castiel under his skin like that. Absolutely not. 

So he got to work.

 

A week later, the work with the big client was pretty much done and Dean still hadn’t talked to Castiel at all. Any work they technically did together was really over e-mail.

As Dean was relaxing in his office, he got a phone call. Zachariah was calling him up to his own office. 

His stomach sank. If Zachariah somehow knew about him and Cas, they could both be fired. There was a fairly strict policy in place that forbade such relations in their office. Too much crap had happened in the past that the most senior heads of the company just banned any and all sexual or romantic relations between employees. Period, end of story.

Dean ran his hand nervously through his hair and rubbed at the back of his neck. 

Rationally, it would be crazy if Zachariah knew. The two of them had been the last two in the building and Dean was positive Cas didn’t tell Zachariah. There was no way that Novak risked his fancy new job. 

Dean made his way up to Zachariah’s office and sat in a plush chair outside of it to wait. Dean was twiddling his thumbs and tapping his foot when Cas walked into the reception-like area outside of the office.

Well shit, Dean thought. If Cas was there then they were definitely screwed. Zachariah knew, he had to.

“Cas,” Dean started, standing up.

Castiel very obviously ignored him because Dean knew he had heard him. The room wasn’t big.

Dean was about to try again when Zachariah’s door flew open.

“Gentlemen,” Zachariah greeted. “Come in.”

Dean found it impossible to read Zachariah’s expression which didn’t help matters.

Without a backwards glance, Cas walked in. Dean followed.

“Have a seat,” Zachariah instructed.

Dean sat to Cas’s right and respected his professionalism. Dean himself felt like he was sweating like crazy and was obvious about what had happened. He felt it written on his forehead clear as day. Cas on the other hand remained cool. If he knew something Dean didn’t about this meeting, he wasn’t letting on.

It wasn’t even distracting enough to look at how nice the office was. Everything was leather, mahogany and very expensive. There was a massive couch, a door to what Dean guessed was a private bathroom and a well-stocked bar.

“Do you know why I called you in today?” Zachariah asked, folding his hands together on his desk.

Dean felt his eyes widen and tried to stay calm. He risked a glance towards Cas who answered “no, sir,” while not breaking eye contact with his boss. Dean cleared his throat and repeated Cas’s answer.

“To cut to the chase, I’m impressed. You two seem to have put aside your differences and have worked remarkably well together. This was a welcome change to how the two of you have interacted in the past.”

“Thank you, sir,” Castiel replied, face still stoic and sitting very stiffly.

Dean only managed a nod and subtly let out the breath he had been holding. Zachariah wasn’t wrong, they really couldn’t be near each other in the past and he had warned them several times to knock it off.

“We’re sending the two of you to a conference with some other members of the company. I, along with some others, feel it will be beneficial,” Zachariah continued. “You’ll have the details sent to your desk by the end of the day but I wanted to tell you all of this in person. You may go.”

Cas thanked him and exited the room. Dean was going to follow him to try to talk to him but was held back by Zachariah.

“I wanted to let you know something, Dean,” Zachariah began. “It was a very tough decision for the promotion. There wasn’t anything you did wrong.”

It was Dean’s turn to thank him and exit the room.

 

That weekend, Dean and Cas were flying halfway across the country for a conference with half a dozen other employees from their company. Dean was definitely not a fan of flying, at all, and he was stuck next to Cas. Of freakin’ course.

Cas who was steadfastly ignoring him despite being less than half a foot away.

“Dude, come on,” Dean tried. “They’re making us share a room. You’re just going to ignore me all weekend?”

The silence was answer enough. Dean put in his headphones and cranked Metallica in hopes of annoying Castiel into telling him to turn it down. The stubborn son of a bitch remained quiet. 

Once they landed and got to their hotel with everyone else, they broke off towards their rooms to put their stuff down. Nothing was scheduled until bright and early the next morning so they had some leisure time. It was already about seven at night when Dean and Cas walked silently into their room. It was big enough to have a couch and table with chairs plus a nice kitchenette in addition to the two queen beds. 

Dean tossed his stuff by one bed and threw the extra room key on the other bed so Cas would have one. Without a word, he went to take a shower. The hot water did wonders to relax him after the stress of flying and Cas being a jackass. 

What a frustrating piece of work, Dean thought.

Everyone on the trip met back downstairs in the hotel’s five star adjoining restaurant for dinner. Cas sat as far away from Dean as possible who told himself he didn’t care. 

After they ate, about half of them stayed around for drinks at the restaurant’s bar. Since Dean and Cas both didn’t want to give up or give in and go upstairs for the night, they both stayed. 

Dean immediately began chatting up a busty blonde who was giggly and drinking martinis while Dean sipped his whiskey. 

Eyes were glaring at him but Dean ignored them. If Cas had a problem, he could get off his ass and tell him instead of continuing his childish silent treatment. Hell, Dean had a half a mind to take this woman up to their room then and now. Cas would be on his own.

Dean was about to suggest something like that to the woman when he finally felt someone clear his throat next to them. 

After he finished what he was saying to her, Nicki or Vicki or something like that, he turned to find Castiel. Everyone else from their company seemed to have left.

“Kinda busy, man,” Dean dismissed. 

“It’s late, Dean. We have a big day ahead of us tomorrow. I think you’re done here,” Cas insisted.

“Oh, he speaks!” Dean exclaimed. “Wasn’t sure you remembered how.”

Cas glared.

“You’re my boss tomorrow. Right now, fuck off,” Dean said. 

He turned back to the blonde who looked a little shocked.

“Don’t mind grumpy here. What were we talking about?” Dean grinned.

That was the last straw for Cas who grabbed Dean’s shoulder and spun him to face him.

“What the fuck?” Dean exclaimed. He had nearly fell off his bar stool at Cas’s forceful grab.

“We’re going upstairs. Now,” Cas snapped.

Not given much a choice, Dean was reluctantly pulled by Cas who had a death grip around his arm.

“Dude, ow. Wanna ease up?” Dean protested.

Cas didn’t answer or lessen his grip.

In the elevator, Cas finally let go of Dean’s arm.

“All right, what gives?” Dean asked. “One minute, you ignore me then the next…”

He was cut off by Cas roughly slamming him back against the far wall of the elevator and claiming his mouth with his own. Dean kissed back just as fiercely without hesitation.

Cas pressed against Dean and kept kissing him until the doors dinged and opened. The two sprang apart. They couldn’t risk anyone from their company seeing them.

Dean took initiative now and grabbed Cas’s arm to take them to their room as quickly as possible. He had wanted to do this again since he left after the first time so he wasn’t wasting any more time.

Once safely in their room, they raced to get each other’s clothes off as if it was the last hour they would have on Earth and they had to hurry. 

Suit jackets landed on the floor, shoes and socks kicked off and ties yanked off and discarded. 

Cas pulled Dean in by his belt loops to kiss him again, only slightly more gently this time. Slender fingers were rapidly unbuttoning his shirt and Dean caught his breath enough to do the same to Cas. 

Shirts finally off, Cas only took a quick second to run a hand over Dean’s chest before pushing him back onto the bed. 

“Damn, Cas,” Dean said, a smile playing on his lips. 

He watched Cas slowly undo his belt and step out of his pants and climb onto the bed and over Dean.

Dean started to undo his belt to free his straining erection but Cas hit his hands away and did it himself. He tossed those aside and kissed Dean once they were gone, pressing his weight down enough to slide their cocks together. Dean broke the kiss enough to mutter something about boxers.

Cas kissed down Dean’s neck softly and sucked bruises when he got to his collarbone. Dean could still see his own handiwork on Cas’s neck and smirked a little. 

“Are we gonna talk about…” Dean started, just as Cas started tugging at the waistband of his boxers. 

Cas lifted his head up and took Dean’s hands to pin them both down above his head. The display of dominance and fierceness in Cas’s eyes had Dean’s dick even harder. 

“No,” Cas instructed. “You’ll only be begging me to fuck you and saying my name. Got it?”

“Yes, sir,” Dean agreed.

Cas reached down and finally did remove Dean’s boxers then his own, sliding their cocks together finally without clothes in the way. 

“Cas,” Dean groaned.

“Good,” Cas smirked. 

“Fuck me, Cas,” Dean said, remembering the other part of the instructions from his boss. 

“Since you asked so nicely and look so damn good…” Cas trailed off, letting his eyes wander down Dean’s body.

Cas hopped off the bed only long to grab lube from his bag.

“Were you hoping this would happen?” Dean couldn’t help but ask.

“Maybe,” Cas answered. “Remember what I told you.”

Dean just nodded.

Cas lubed up one finger and wasted no time getting to work. 

“Fuck,” Dean arched his back as Cas entered him.

Cas kept working him open. When he had two fingers, he added his mouth slowly sliding up and down his cock and it was almost enough to drive him over the edge. 

“Cas, come on. Hurry up and fuck me.”

Cas found his prostate then and crooked his finger enough to have Dean throw his head back and gasp for breath.

“Holy fuck…”

“You’re not going to be nearly as frustrating as you usually are when I’m pounding you into the mattress,” Cas said.

“Yes, please. Cas…” 

Cas added a third finger and continued to gently mouth at Dean’s throbbing erection. A few minutes more and Cas figured Dean was ready.

“Flip over,” Cas demanded. 

Dean listened immediately. 

He could hear Cas open a condom he must have grabbed with the lube. There was a pause as he put it on and coated himself in lube.

“Please, fuck me. Want you so bad,” Dean said, slightly mumbling with his face in a pillow.

“Do you know how infuriating you are?” Cas asked.

Without waiting for an answer, he cautiously eased himself inside Dean until he was fully seated.

“You feel so good, filling me up,” Dean said. “How am I infuriating?”

He wasn’t sure it was the right conversation to have while Cas’s dick was buried in his ass but if that’s was Cas wanted, then fine. 

“You fuck me in my office,” Cas said, easing back out just enough. “Then just leave.”

At the word “leave,” Cas slammed full force back into Dean. He would have collapsed if Cas didn’t have a bruising grip on his hips. 

“So of course I ignore you. I was pissed,” Cas said, pulling out almost all the way. “Then, I have to watch you flirt with that woman downstairs.”

He slammed back in again and Dean let out a moan he knew someone from their company had to have heard in their room. 

“Shit, Cas,” Dean said, “I didn’t realize…”

“Didn’t realize? Didn’t realize how ridiculously attractive you are, how good you made it for me last time? How all I want to do at work is rip your damn clothes off?”

“Fuck,” Dean groaned. “Cas, harder. I know you can do better.”

That remark, Dean knew, would be what Cas needed. He started a pace of rough thrusts, consistent and hard. 

“That’s it, baby,” Dean encouraged. 

He ignored what Cas had explained, for now. He could worry about that after he had a mind-blowing orgasm he knew his boss could give him.

Cas shifted just enough and found the right spot to make Dean see stars. 

“Holy shit, you’re so good, feel so good, Cas. Getting close. You gonna make me just come on your cock?”

That was exactly Cas’s plan and he quickened his already intense pace and reduced Dean to a groaning mess. 

Cas was close, real close, and knew he could make Dean come without touching his cock.

“Dean, come for me. Just from my cock, you know you love being filled up by me. Go ahead, let go.”

A few more thrusts from Cas had each of them coming, Dean making a mess under himself and Cas inside Dean. 

Cas added a few more thrusts to ride it out before he pulled out. Dean was careful to flip onto his back away from the mess he made and his eyes were closed with a smile on his face.

Cas got a towel from the bathroom after he threw the condom out and came back to clean the bed a little before tossing it back towards the bathroom.

“This one’s ruined. Might as well share the other one,” Dean grinned, eyes still closed.

“Fine,” Cas agreed.

Neither of them cared about the implications of cuddling after sex in that moment. They could deal with that tomorrow.

He pulled Dean up by the arm and over to the other bed. Cas landed on his back and Dean sort of crashed on top of him. He slid off just enough so Cas wasn’t being smothered but stayed pressed against Cas’s side with an arm draped over his stomach.

Without another word, they fell asleep.


	3. Christmas Party

**Summary for the Chapter:**

> The company Christmas party, where jealousy and smut ensue. 
> 
> Thank you to the lovely commentor, akibabes25, who gave me the idea to add Benny. You are the best!

To say the next morning was awkward would have been a massive understatement. Dean woke up with his face pressed against Cas’s chest and his arm still over his stomach. 

“We should, uh, probably get dressed,” Cas suggested when he realized Dean was awake. 

“How long have you been awake?” Dean asked, slowly remembering the night before.

“Not long,” Cas replied. “But we already had to be up early so I saw no reason to cut your sleep even shorter.”

Dean pulled himself off of Cas and sat up. Cas had a just the smallest hint of a smile on his lips. 

“What?” Dean asked.

“Your cheek, it’s all red…it’s nothing.”

Cas looked away and his own cheeks got a little red. 

Dean put his hands to his face and one cheek was definitely warm, the one that had been against Cas’s chest all night. He would be lying if he said that hadn’t been nice. Honestly, he hadn’t slept that well in a while.

“I’m going to take a shower.”

Cas said that as he hurried into the bathroom.

At least we’re talking after, Dean figured. It was already an improvement from the last time.

Dean sat on the bed and thought about why it was so awkward between them. The sarcasm and ruthless flirting was gone and was replaced by careful sidestepping and shy eyes but he didn’t understand why.

Sure, they had woken up cuddled together. But Cas got pissed the last time when Dean had left. It didn’t make a whole lot of sense and Dean was getting whiplash. He also had a minor headache from the whiskey he drank the night before which wasn’t helping his thought process.

Cas came out of the bathroom in just a towel and Dean kept his eyes focused anywhere else. It seemed like they were on good terms but just not talking about the fact that the sheets on one bed still had a stain from Dean’s come.

Dean took a quick shower as well and brushed his teeth. When he came out of the bathroom to get dressed, Castiel was already gone. 

Well okay then, Dean thought. We’re not talking about it then.

 

The day-long conference went well on a professional level but Dean and Cas were still avoiding talking about anything substantial. The two of them acted like acquaintances that had nothing more to say to each other than to comment on the weather when that was far from the truth. 

Their second and already final night there, Dean stayed for drinks again but only talked to his colleagues from his company. Cas turned in early and was supposedly asleep when Dean came to the room sometime later. The sheets had been changed, thankfully, and Dean crashed on the other bed.

On their last morning, Cas must have already gone downstairs when Dean woke up as the room was empty.

Dean packed up and made sure to do a final sweep of the room to make sure neither of them had forgotten anything. Cas’s watch was still on the nightstand. Dean took this as an opportunity to talk to Cas since he had to hand to back.

“Cas, hey,” Dean greeted once he joined everyone in the lobby. 

They were waiting for their shuttle to their airport. Dean was still trying very hard not to think about the flight he had to take and used Cas as a distraction.

“Hello, Dean,” Cas said, not sounding as stiff as the words would seem.

“You forgot your watch,” Dean said, holding it out.

“Oh, thank you,” Cas answered, accepting it and putting it on. “It would have been a shame to lose it. It was a gift from my uncle.”

Dean nodded and didn’t know what else to say. 

They sat next to other people on the bus but were next to each other on the plane again. Since they were a somewhat last minute addition to the trip, their seats were away from their colleagues. Dean seized the opportunity.

“So, are we going to talk about this or no?” Dean asked.

“Talk about what?” Cas asked back, flipping through the SkyMall magazine.

“The fact that two days ago, you weren’t saying anything to me and now you’re treating me like just another coworker even though we fu…”

“Yes, we did,” Cas agreed and cut Dean off, “but we work together and you know the rules.”

“You didn’t care about the rules the other night,” Dean couldn’t help but point out. 

“Well, now I do. While I’m glad we’re not constantly bickering or fighting like children, nothing like that can happen again. I care about my job even if you don’t.”

That pissed Dean off and he turned to pretty much the only thing that calmed down during a flight, his music. He tuned Cas out and just listened to Led Zeppelin.

How could Cas fly into a jealous, albeit sexy, rage and fuck him into the mattress and then just essentially pretend it didn’t happen? Dean almost wanted to say he preferred how things were between them before they ever did anything but he knew that would be a lie. Getting to be with Cas had been amazing but it seemed like they were done before they had a chance to be anything more.

 

A month after the business trip, Dean and Cas worked together but didn’t speak much outside of anything professional. Cas wanted to repeat what they had done in the past but had to respect what he said and couldn’t go back on his word. He really didn’t want to lose his job and he and Dean had been getting along really well. Cas didn’t want to ruin that either. 

One afternoon in mid-December, Cas called Dean up to his office to get a brief update on the current project they had been assigned. It was formal and stifling and Cas wanted nothing more than to get fucked by Dean on his desk again. Castiel had an idea once Dean was prepared to leave.

“That’s about it,” Dean said, “If we’re good, I’m going to head downstairs for lunch.”

“I can have stuff brought up here if you wanted to stay?” Cas asked uneasily.

“Sure,” Dean smiled. 

Cas let out the breath he held waiting for a response.

So maybe they could try being friends. Friends who had previously fucked and still jerked off using those memories, at least Cas did. He couldn’t speak for Dean and if he did but that was hot to think about, Dean slowly pumping himself over the edge as he remembers the fun they had…

“Cas?” Dean asked.

“Uh, what?” Cas asked, caught daydreaming about his subordinate rubbing one out.

“I was saying what I wanted to eat.”

The two of them ordered and they sat and talked while they waited for their food. They talked a little about what they did outside of work. Cas was a fan of gardening and reading while Dean was more into mechanical work on his car and playing guitar. Just as they were getting into their families, food long finished, there was a knock on the door.

“Yes?” Cas called. 

His assistant came in and said there was someone here to see a Mr. Winchester. 

“Downstairs sent him up,” he explained.

“Thank you, let them in,” Cas said.

Dean’s face seemed to imply he had no clue who could be visiting him at work.

The door opened and in walked a tall and slightly intimidating man with an old-fashioned hat and a stubbly beard. Cas had to admit he was an attractive guy.

“Benny?”

“Hey, Dean. How ya doin’?” the man replied in a deep, Southern drawl.

Dean stood up and gave Benny a tight hug. Maybe Cas was just jealous but it seemed to go on for a while.

“Oh, right. This is my, uh, boss. Cas,” Dean introduced. “Cas, this is my friend Benny.”

“Nice to meet you,” Cas answered without a smile. 

“You too,” Benny answered. 

“What are you doing here?” Dean asked.

“I was in town, figured I’d look you up,” Benny replied. “They told me I could find you up here.”

“I’m glad you did, it’s been too long,” Dean said.

Neither man had stopped smiling since Benny had walked in and Cas had the distinct impression that they used to date. The way they looked at each other was clue enough and the long hug plus they were standing maybe just a little too close to each other. Benny had extremely blue eyes and Cas figured Dean had a thing for them.

“Well, I have to get back work but it was nice to meet you Benny,” Cas stated.

Dean took the hint and ducked out of Cas’s office after Benny without a word to Cas. It wasn’t hard for Cas to overhear them making dinner plans for when Dean was done with work.

Castiel mentally kicked himself for being so stupid. Of course Dean would have other people interested in him, the man was insanely handsome. God, it wasn’t even just that or the fantastic sex. He was smart and funny and…

Stop, Castiel scolded himself. You told him nothing more could happen. You aren’t being fair.

Screw fair, though. Castiel wanted Dean even if that jeopardized his career.

 

Less than a week after Benny’s visit, the company was hosting their annual Christmas party. Most people brought girlfriends, boyfriends or spouses. Castiel, as usual, was going alone.

Once work was over early on the Friday before Christmas, Cas joined everyone. The party was in the enormous multi-purpose room they had. It usually hosted intellectual or motivational speakers or large important presentations and was designed to fit the entire company. It was decorated for the theme, had plenty of food and drink, and a lot of people were dressed for the holiday. A good amount of women had red or green dresses and some of the men had changed into ugly holiday sweaters.

Cas immediately spotted Dean despite the size of the room and was not surprised to find that he was talking to a group of three women from the HR department. Cas shook his head. He assumed Dean would bring Benny but didn’t want to look around and see him.

At the booze table, Cas made himself with a generous amount of alcohol in it.

“That kind of day?” 

Cas turned to find Meg, the head of the HR department, standing with her arms crossed and a wry grin on her face. Her dark hair went along with her black dress.

“Hello, Meg. The day has not been ideal,” Cas explained.

“Cheer up,” Meg advised. “No more work for the rest of the year.”

“That’s a fair point, but…”

Castiel couldn’t help his eyes trailing over to where Dean was still chatting up the women and making them laugh. He took a long drink.

“Now, now. You know that isn’t allowed,” Meg pointed out.

“Believe me, I know,” Cas replied forlornly.

While they were only sort-of friends and not that close, she did seem to be able to read Cas pretty well.

“I might be able to help, though…”

“How?” Cas asked, wary of her help. He took another drink.

While Meg could be helpful and kind at times, she also had a history of manipulation.

“You can use me to make Dean jealous,” Meg suggested.

“That wouldn’t work. You’re head of HR and he knows we can’t date because of the company policy, that’s even what I told him.”

“Perfect,” Meg grinned.

Somehow, her grin was not reassuring. In fact, it made Cas take another drink.

Cas squinted his eyes and tilted his head, not getting what was perfect.

“How pissed will he be if you’re with me? Like you said, I’m head of HR and you would be ignoring the same policy you said kept you two apart. If he gives a shit about you, this will make him snap. Got it?”

Cas nodded.

“Follow my lead.”

After Cas downed the remainder of his drink, he allowed Meg to grab onto his arm and steered them towards Dean. Cas started to feel a slight buzz from his drink. He did not drink often and that drink he made packed a punch.

As they walked up, Cas watched Dean’s smile falter as he noticed Meg on his arm. Cas tried very hard not to grin at that. Meg might have had a point.

“What’s going on here?” Dean asked.

“Oh, nothing. Cas here was just taking me to his office for a drink. Nothing here suits my fancy,” Meg said.

“Really,” Dean scoffed, glaring at Cas.

Cas could only nod.

“You seem to have your hands full here, so we’ll leave you to it,” Meg said, gesturing at the women who were still hanging around.

“Hold on,” Dean snapped as Meg started to pull away.

Cas cracked a self-satisfied smirk before turning them both around with an annoyed face.

“Can I talk to you for a second?” Dean asked, quietly but Meg still heard.

“Fine,” Meg said, “find me if you’re bored later.”

Cas watched her go over Dean’s shoulder and held back a smile as Meg winked. He owed her big if this panned out.

Dean stepped closer to the door and Cas followed. This wasn’t a discussion to have by anyone else.

“What is it, Dean?” Cas asked, crossing his arms. 

“You can’t do that,” Dean said, crossing his arms as well. 

Cas couldn’t help but laugh. Dean looked and sounded like a child.

“What the hell is funny?” Dean snapped.

“You. You’re funny,” Cas answered with a shrug. “I try to leave with someone and you get pissed when you have no problem flaunting your three women in front of me!”

“Flaunting? Really? You want to talk about flaunting? So, it’s a coincidence you’re sneaking off with the HR director and you have to talk to me? Try to make me jealous?” Dean countered.

Cas didn’t point out that it was obviously working, making him jealous.

“Whatever, Dean. Don’t you have some big lumberjack to get home to? Benny?”

“Is that what this is all about? You got jealous because of Benny? Holy shit, Cas. We dated like a million years ago, we’re cool now. I can’t believe you thought…”

“Can you blame me?” Cas asked, quiet enough that Dean almost missed it.

Dean paused, his face relaxing and eyes becoming gentler. Cas had never really seen that side of Dean. They both uncrossed their arms.

“Do you actually have booze up in your office?” Dean asked softly.

“No,” Cas grinned, blowing the cover of his ruse with Meg.

“You son of a bitch,” Dean grinned back. “Luckily for you, I do. Come on.”

 

While Dean’s office was not as big or as nice as Cas’s, it still had a couch. Dean poured them a couple of drinks and they were able to lose their suit jackets, ties and shoes and relax.

“You know,” Cas said as they began a second round, “I think that rule is stupid.”

“What rule?” Dean smirked knowingly.

“The one that says I can’t make out with you on this couch and then suck you off.”

“Jesus, Cas,” Dean breathed, eyes dropping to Cas’s lips. 

Cas carefully set his glass down on the table and leaned into Dean’s space.

“You forgot a coaster…”

“Shut up.”

Cas shut Dean up by kissing him softly, less rushed and frantic than they had ever before. They had time, neither of them were going anywhere soon and Cas wanted to finally take his time. Cas moved onto Dean’s lap to straddle him, caressing Dean’s face as he grabbed Cas’s waist.

Fingers delicately found buttons and gradually undid them. Their shirts were tossed aside and Cas rolled his hips against Dean’s, feeling how hard he was. The layers of clothes were in the way but Cas was going slow. 

Cas kissed down Dean’s neck without a lot of pressure until he reached his collarbone and sucked a mark there. He used his mouth and fingers to tease Dean’s nipples one at a time.

“You’re killing me, Cas. Need more,” Dean said, his voice needy.

“I’m keeping my promise, don’t worry,” Cas responded.

He undid Dean’s belt buckled and undid his pants. Dean lifted his ass up to push them and his boxers down. Cas slid off of Dean to kneel in front of him. He pulled the clothes the rest of the way down and threw them to the side. Dean was only in his socks but Cas got rid of those, too.

Cas slid his hands up Dean’s thighs and stopped to grip his hipbones.

“Gonna suck me off, Cas? Take all of me down?” Dean asked.

Cas’s answer was to give Dean’s cock a few strokes with his hand, making sure he was hard and he was. Cas enjoyed the fact that he hadn’t done much to get Dean this worked up.

Cas licked a stripe up the underside of Dean’s dick without warning and Dean practically screamed Cas’s name. Without stopping, Cas mouthed at the head, tonguing over the slit and tasting the precum that was already there. He eased his mouth down a little farther, relaxing his jaw and easing back up. It didn’t take long to get a steady rhythm going.

“Fuck, Cas. Close, I’m…close, baby. Cas, don’t…don’t stop,” Dean groaned, breath catching.

Cas hummed along Dean’s dick as he sucked and bobbed, adding a hand to massage his balls.

Dean’s hands were tight in Cas’s hair and tightened as he got closer to the edge. Cas kept his mouth at the head and jerked Dean through his orgasm, swallowing it all down.

“Cas, oh my god,” Dean panted. “You are too good at that.”

Cas grinned, allowing himself to take pride in taking Dean apart like that. Cas sat on the couch next to Dean.

Once Dean caught his breath, he offered to the return the favor.

“You don’t have to…”

“I want to,” Dean said, eyeing the obvious bulge in Cas’s pants.

Cas wasn’t about to argue.

Dean repeated what Cas did and climbed into his lap. He kissed him and could taste his release still on Cas’s tongue. He chased the taste, exploring his mouth, and enjoying the feeling of how dirty he should find it. Dean rolled his hips, feeling how hard Cas was.

“I’m going to take care of you. Did you know I didn’t even lock the door?” Dean said, dropping to his knees. 

Cas couldn’t care enough to panic. Dean was about to suck him off and was not doubt amazing at it. There was no way he was stopping for anything.

“That’s hot, isn’t it?” Dean continued. “Knowing anyone could walk in, see me naked on top of you? Or maybe they could walk in when your dick is all the way down my throat.”

“Fuck, Dean,” was all Cas could manage.

Dean got Cas out of the rest of his clothes before swallowing Cas down in one go. Cas was right, the guy had experience and damn was he good. Watching Dean come had Cas on edge already but his mouth and hand were magic, doing all the right things and making Cas moan.

It didn’t take long for his hand to tighten almost painfully in Dean’s hair as the only warning before he was coming down Dean’s throat with a shout of his name.

“You’re so vocal when we do this,” Dean praised, joining Cas on the couch.

“I’m usually not. It must just be you,” Cas said, eyes closed in post-orgasm bliss.

Dean tried not to think too much of the implications what Cas said.

“You know we can get fired,” Dean said.

It was tight but they maneuvered to lay down together, Cas curled on his side against Dean’s side who was on his back.

“They can’t fire me,” Cas boasted.

“Oh, because you just got promoted and are so important?” Dean teased.

“And pretty much my whole family works here.”

“What?” Dean asked, confused.

Cas kept going without thinking.

“They do. Zachariah? He’s my uncle.”

“He…what? Are you fucking kidding me?” 

Dean sat up abruptly, causing Cas to fall on the floor.

“Dean, what?” Cas asked, standing up and not getting why Dean was upset.

“Guess that explains how you got promoted,” Dean said, turning his back on Cas.

“Dean, that’s not fair.”

“Get dressed and get out.”

“Dean…”

“It’s that or I throw you out naked. Go.”

Cas got dressed as quickly as he could.

At the door, he said a soft “I’m sorry” and he wasn’t even sure if Dean heard him.


	4. The One Where It All Works Out

Dean couldn’t believe he had been so stupid. After Cas left, Dean waited until he was out of earshot before whipping both of their glasses from their drinks at the wall. One smashed, then the other, but Dean didn’t feel any better.

Of course Castiel wouldn’t go into this without some insurance, Dean seethed to himself, he was too smart for that. If he couldn’t get fired then he had nothing to lose. His plan must have been to rip the promotion out from under Dean and then get him fired. The man had gotten past their petty rivalry or had just taken it to the extreme.

It worked so far.

Hell, Castiel could have been on the phone with Zachariah telling him the whole story getting Dean fired.

Dean grabbed a cab home. Between the alcohol and anger, he was in no state to drive. Once at home, he was out like a light. He was expecting his mind to keep running a mile a minute but he was out when he his head hit the pillow. 

The next day sucked. His head hurt and his body ached like he had run a marathon. Despite that, he had to combine running and walking to get his car. No matter how much he drove around, listened to music or exercised, he could not stop thinking about Cas. Every time he did, he wanted to throw things again.

Since the company was so successful, they had from a couple days before Christmas until a few days into the New Year to relax and not come into work. It was like winter break from school all over again. Unfortunately, that just gave Dean more time to think about Cas and the last conversation they had but at least he didn’t have to see him. There was no guarantee he wouldn’t punch him in the face if he did. Normally, Dean did stuff to relax since work was usually stressful enough. This was not helping the situation. 

How could Cas not mention that his family practically owned the company and how could he not get that Dean was pissed? It was bullshit. Dean was half-expecting an e-mail from Zachariah about his immediate termination once Castiel finally spilled. Before this went down, Dean would have admitted he trusted Cas. Now, he wasn’t so sure. Family was important, Dean understood that.

 

The day before Christmas, Sam was set to arrive from California with his new girlfriend, Madison. Dean’s phone rang and it was a number he didn’t know so he figured it was maybe Madison saying they had landed. 

“Hello?” Dean answered.

“Dean? Don’t hang up, it’s me. It’s Cas.”

Dean did exactly that and hung up. There was no way he was talking to him. His brother was flying in and Christmas was a day away. He didn’t need anything to dampen his mood. Dean tried his best to keep a happy face and hugged Madison and Sam before helping them get their stuff into the car. 

 

Christmas was the usual affair, time spent with family, and normally Dean enjoyed Christmas. This year, he couldn’t help but be a little sour while everyone got together at Bobby and Ellen’s.

“All right, enough,” Ellen snapped. “What’s eating at you, Grinch?”

She was the woman who helped raise him with her husband, Bobby, and could read him like a book. They were alone in the kitchen and she cornered him while he was finishing the mashed potatoes.

“Nothing,” Dean lied.

Ellen whacked the back of his hand with a spoon.

“Ow! Jeez, Ellen,” Dean complained. “Fine! It’s drama with someone at work. I thought they liked me and they don’t. I just need to stop being a whiny bitch about it and it’ll be fine.”

“Is it this boss of yours that Sam mentioned?” Ellen asked. 

Dean nodded.

“Dean Winchester, did you sleep with him?”

He could feel his face get warm and Ellen took that as answer enough.

“Fool move but I hope it works out. These kinds of things usually do. Now, help me get our masterpieces onto the table,” Ellen said.

The two of them brought all of the dishes they worked hard on preparing to the table. The seven of them sat down and enjoyed the delicious meal. 

Dean loved his family, he did, and he was happiest when he was with them but it just felt like something was missing. Ellen had Bobby, Sam had brought Madison and even Ellen’s daughter Jo brought a new man, an FBI Agent no less. Dean didn’t like him at first but he felt like they could get along eventually. Problem was that Dean was the odd man out.

So maybe it wasn’t something as much as someone was missing. Dean was just lonely even though he was surrounded by those he loved. He repeatedly thought of calling Cas. He knew his family had to all be stuck-up and boring and wanted to spare him.

But he also still wanted to punch him.

 

New Year’s was more of the same. At the bar that Ellen owned, the Roadhouse, there was a party. Dean couldn’t help but feel weighed down by the same nagging feeling he had at Christmas like not everyone was there. Seeing all the couples just made him miss Cas so he decided he needed to find someone. That kind of thinking was ridiculous but he didn’t care. He didn’t need the lying son of a bitch, or that’s what he kept telling himself.

After a few more drinks, he started hitting on the few single ladies that were there. He was drawn to one with long, dark brown hair and blue eyes. He was just drunk enough not to figure out why he picked her.

As they made out in the hallway to the bathroom, Dean realized he couldn’t do this. He stopped and took a step back.

“I’m sorry, I can’t,” he muttered. 

Without a word to anyone, he slipped outside and hailed a cab. Once at home, he turned his phone off and drank until he passed out. 

He didn’t even make it until midnight.

 

After he finally woke up around noon and called everyone back to reassure them he was fine, he just hadn’t felt good, he was sorry he didn’t tell them he was leaving, and all that, he fell back asleep.

The year was off to a shitty start. 

Dean didn’t move much that day, except to go to the couch to watch reruns of Dr. Sexy and order some pizza. In the back of his mind, he knew he was being pathetic but he didn’t care. His phone rang and it was the number Cas used before.

Dean ignored it and it didn’t ring again.

 

The next day was his last day off before returning to work. Dean’s stomach got twisted with nerves when he thought of the prospect of returning to the office and seeing Cas. There was no way of knowing how it would go. Maybe Zachariah had been trying to get Castiel to deliver the news that Dean was fired personally. It sounded like Dean’s luck.

He hung out with Sam briefly as he would be flying back the next day. Jo and Ellen offered to take Madison to lunch, which meant interrogating her since she was now dating Sam, so Sam came to Dean’s alone.

“You know, I’m worried about you,” Sam said as they ate the leftover pizza.

“Me? Why?” Dean asked, “I’m right as rain.”

“Sure,” Sam rolled his eyes. “That’s why you’ve been moping the whole time I’ve been here. What happened?”

Dean could tell Sam was not going to let this go so he finished his piece of pizza before starting at the beginning. How Cas had gotten the promotion and they had to work together. He spared Sam the exact details of what happened in Cas’s office but did say that he left after they fooled around. Dean got into the fight, the trip, the hotel, vaguely mentioning they fucked again and then the Christmas party. All of it culminating to the fact that Cas lied and was a manipulative bastard. 

“I don’t know,” Sam said with his eyebrows furrowed together. 

“You don’t know what?” Dean snapped. 

“I don’t know that Cas was manipulating you. Yes, he should have told you that Zachariah is his uncle but if he wanted you fired, he would have done it after the first time anything happened.”

“So he actually wanted to sleep with me?” Dean asked, genuinely shocked.

“I think this goes beyond the sex, Dean,” Sam said, a little exasperated.

“Like, feelings?”

“Oh my god, you’re not a caveman. Yes, feelings,” Sam said, throwing his hands in the air. 

“Oh,” Dean said, in a small voice.

“I know I’m being harsh but you need to hear this. You were upset at Christmas and New Year’s and I think this might be why. I think you wanted Cas to be there,” Sam inferred.

Dean looked down and didn’t answer, which was answer enough to Sam. 

“Just tell him,” Sam advised with a shrug. 

“What if he doesn’t feel the same way?” Dean asked, still looking down. 

“Oh, he has to. You’ve told me than I needed to know, honestly, but I think he does. The way he got so jealous at the hotel?” Sam pointed out.

Dean thought about it and figured it was a good point but something had to change. They couldn’t keep an actual relationship secret. What they were doing before was hard enough to keep on the down low. If Cas felt the same way though, it would be worth it. 

“I have to quit,” Dean said, kind of shocking himself with that realization.

Sam grinned, proud of his brother for finally following his heart and doing something for himself for once. 

 

 

The next day, Dean was at work and more nervous than any other time. The prospect of seeing Cas now freaked him out and what he was about to do was another problem.

He told Zachariah’s secretary he was there for his appointment and sat down. 

After all the time he had put into this place, he was almost sad to see it go. But he needed to quit. If he quit, he could be with Cas. Sam helped him realize what he had felt for… who knew how long. Maybe Dean had started a petty and childish feud with Castiel to cover his real feelings all along because he was afraid of getting hurt or being in a relationship or whatever. He also came to realize that Cas didn’t mention who his family was, especially Zachariah, because he knew how would it look after the promotion and Dean would have never slept with him. Dean understood, he just needed to tell Cas that but after he took care of something else.

Enough psychoanalyzing Dr. Phil crap, Dean thought, when would Zachariah…

“Dean?”

Dean’s head snapped up at the familiar voice.

“Cas, I…”

“I’m sorry,” they said together.

“I should have…” Dean continued.

“I didn’t…” Cas tried at the same time Dean spoke.

There was a brief pause.

“All this time, we were a couple of dumbasses, huh?” Dean asked with a shy smile.

Cas smiled back and stepped closer to Dean. Then he got a confused look on his face.

“Dean, why are you outside of Zachariah’s office?”

“I’m here to quit,” Dean said, like it was obvious. “Why are you here?”

“The same reason,” Cas answered, still looking confused. “But…”

“I did a lot of thinking over the time off we had and got to thinking about my life,” Dean explained. “We can’t be together if we work here and honestly, it’s not really what I want to do with my life. Then thinking about my life and what I wanted…I kept picturing you, Cas.”

“Dean,” Cas said, softer and with more feeling than anyone had ever said his name before.

Cas reached out to cup Dean’s face gently in his hand. Dean sighed and leaned into the touch before something dawned on him.

“Cas, how were you going to quit? Your family…”

“I don’t love this job. I love you. And if my family stands in the way, they can bite me,” Cas smiled.

“I…you? What?” Dean asked, a little taken aback. 

Cas’s face fell a little and he dropped his hand. Dean instantly regretted what he said and wanted Cas’s hand back on his face. This was new and scary and wonderful and Dean had never felt better. He had no doubt in his response.

“No, Cas…I…You took me by surprise is all,” Dean grinned. “I love you, too.”

Cas smiled again, wider than ever and all gums. Dean couldn’t help but grab Cas’s face and kiss him. He didn’t want to stop but after a minute he had no choice.

“Dean- What is the meaning of this?” Zachariah snapped, finally opening his door.

The two stopped kissing and took a step back. Zachariah looked angrier than either of them had seen him but the two of them held their ground.

“We can explain,” Dean smirked before glancing at Cas.

“We quit,” Cas said, eyes not leaving Dean’s face.

“You can’t…Castiel, I swear to you if you…” Zachariah started to threaten.

“Don’t even think of finishing that sentence,” Dean glared back at him. “We’re out of here.”

Cas grabbed Dean’s hand and led him away from his uncle who began to spew profanities and threats, all of which went over their heads. 

Dean and Cas made their way out the front door of the skyscraper they had wasted so much of their lives in already. Neither of them had really kept anything personal in their offices so were fine leaving it all behind without a backwards glance. The future was looking pretty bright.

“At least one good thing came from working there,” Cas observed as they walked down the street hand-in-hand.

“Yeah?” Dean grinned, glancing at Cas and guessing where he was going.

“The view from my office was just… amazing,” Cas said, positively beaming at Dean.

Dean playfully whacked him on the arm.

“You know I meant meeting you, Dean.”

“I know,” Dean agreed. “What do you say we get something to eat?”

They found a little hole in the wall diner for an early lunch. Since they were both jobless, they discussed what they wanted to do. Cas liked teaching or writing. Dean also considered teaching but loved the idea of being a mechanic or firefighter too. 

Turns out, the two of them didn’t end up eating much. Part way through the meal, Cas had been getting too adventurous with his game of footsie so Dean dragged him to the bathroom. 

Dean prepped Cas quick and was sliding in, easily getting them to both come in what would normally have been an embarrassing amount of time but they were in a hurry. Dean couldn’t hold back having Cas in front of him, hands braced on a bathroom stall, moaning his name as he fucked into him. The fact that he could leave hickeys anywhere he wanted was a bonus, too. he definitely took advantage of that.

Apparently, Cas had been moaning Dean’s name a little too loudly because the whole restaurant seemed to be looking at them when they came out of the bathroom. It wasn’t much longer that the manager asked them to leave.

Dean couldn’t help but laugh as he paid and left an insanely generous tip. Seeing Cas with his red, swollen lips, sex hair and obvious hickeys and knowing he looked the same cracked him up. This would be quite the first date story. Dean told Cas that under his breath and Cas hit his arm.

The two of them continued to laugh and smile as they again walked the street hand-in-hand. 

“Where to, Cas?” Dean asked.

“Anywhere we want, Dean.”

**Notes for the Chapter:**

> Thanks for reading, hit me on the tumblr it's the same name as on here!


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